European Patent Application (EP-A) No. 83,975 (published July 20, 1983) discloses herbicidal benzenesulfonamides of formula ##STR1## wherein Q is selected from various five or six-membered aromatic or partially unsaturated heterocyclic rings containing 2 or 3 heteroatoms selected from O, S or NR.
EP-A-85,476 (published Aug. 10, 1983) discloses herbicidal benzenesulfonamides of formulae ##STR2## wherein Q is selected from various 5-membered aromatic heterocycles, and their dihydro and tetrahydro analogs, which contain one heteroatom selected from O, S or NR, or Q is a saturated or partially unsaturated 6-membered ring containing one heteroatom selected from O or S; and
Q.sup.1 is a 6-membered aromatic heterocycle containing one to three N atoms. PA0 B and C are independently H, halogen, NO.sub.2, C.sub.1 -C.sub.8 alkyl, CO.sub.2 R, etc.; and PA0 D is H or C.sub.1 -C.sub.8 alkyl. PA0 Q is an unsubstituted or substituted five-membered heterocyclic radical which is bound by way of a carbon atom and which contains 2 or 3 identical or different heteroatoms. PA0 C is --CO--, CR.sub.21 R.sub.22 or --SO.sub.2 --; and PA0 n is 0 or 1. PA0 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, amino, C.sub.1 -C.sub.3 alkylsulfonyl, CO.sub.2 R.sup.III, C.sub.1 -C.sub.3 haloalkoxy, C.sub.1 -C.sub.3 haloalkylthio, CH.sub.2 CN, CH.sub.2 OCH.sub.3, or CH.sub.2 SCH.sub.3 ; PA0 R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA0 R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA0 R.sup.I and R.sup.II may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA0 R.sup.III is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.2 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA0 M is H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, phenyl, phenyl substituted with Cl, NO.sub.2, CH.sub.3 or OCH.sub.3, C.sub.2 -C.sub.3 alkoxycarbonyl, C.sub.1 -C.sub.3 alkylsulfonyl or SO.sub.2 NR.sub.4 R.sub.5 ; PA0 Q is ##STR10## G is C.dbd.O or SO.sub.2 ; W is O, S, CHR.sub.2 or NR.sub.3 ; PA0 W.sub.2 is O, S, SO.sub.2, CHR.sub.2 or NR.sub.3 ; PA0 R.sub.2 is H, C.sub.1 -C.sub.2 alkyl, Cl, F or Br; PA0 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.2 -C.sub.4 cyanoalkyl, C.sub.3 -C.sub.4 alkenyl or C.sub.3 -C.sub.4 alkynyl; PA0 E and E.sub.1 are independently C.sub.3 -C.sub.4 alkylene, C.sub.3 -C.sub.4 alkenylene or C.sub.4 alkenyldienyl; PA0 E.sub.2 and E.sub.4 are independently C.sub.1 -C.sub.2 alkylene or C.sub.2 alkenylene; PA0 E.sub.3 and E.sub.5 independently are C.sub.2 -C.sub.3 alkylene or C.sub.2 -C.sub.3 alkenylene; and PA0 E, E.sub.1, E.sub.2, E.sub.3, E.sub.4 and E.sub.5 may optionally be substituted by 1-4 groups selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkenyl, OH, halogen or C.sub.1 -C.sub.4 haloalkoxy; further, when W is O, CHR.sub.2 or NR.sub.3, one of the carbon atoms of E may be in the form of a carbonyl group, and when W.sub.2 is O, CHR.sub.2 or NR.sub.3, one of the carbon atoms of E.sub.4 or E.sub.5 may be in the form of a carbonyl group, provided that said carbonyl groups are not bonded directly to G; PA0 A is ##STR11## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA0 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, C(O)R.sub.6, ##STR12## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA0 L.sub.1 and L.sub.2 are independently O or S; PA0 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.2 alkyl; PA0 R.sub.6 is H or CH.sub.3 ; PA0 Z is CH or N; PA0 Y.sub.1 is O or CH.sub.2 ; PA0 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA0 Y.sub.2 is H or CH.sub.3 ; PA0 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA0 Y.sub.3 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; and PA0 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA0 (a) when G is SO.sub.2, then W is O, CHR.sub.2 or NR.sub.3 ; PA0 (b) when E.sub.2 or E.sub.4 is C.sub.2 alkylene or C.sub.2 alkenylene then E.sub.3 or E.sub.5 is C.sub.2 alkylene or C.sub.2 alkenylene; PA0 (c) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA0 (d) when M is other than H, alkyl, alkenyl, alkynyl or phenyl, optionally substituted, then R.sub.1 is H, alkyl, haloalkyl or halogen; PA0 (e) when X or Y is OCF.sub.2 H, then Z is CH; PA0 (f) when the total number of carbon atoms of X and Y is greater than four, then the number of carbons of R.sub.1 is less than or equal to two and the number of carbons of Q is less than or equal to eight; and PA0 (g) when W.sub.1 is S, then R is H, A, is A-1, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR13## PA0 (1) Compounds of Formula I where PA0 (2) Compounds of Preferred 1 where PA0 (4) Compounds of Preferred 2 where Q is Q.sub.2 ; PA0 (5) Compounds of Preferred 2 where Q is Q.sub.3 ; PA0 (6) Compounds of Preferred 2 where Q is Q.sub.4 ; PA0 (7) Compounds of Preferred 2 where PA0 (B) Compounds of Preferred 7 where PA0 (9) Compounds of Preferred 8 where PA0 (10) Compounds of Preferred 9 where PA0 (11) Compounds of Preferred 10 where Q is Q-1; PA0 (12) Compounds of Preferred 10 where Q is Q-2; PA0 (13) Compounds of Preferred 10 where Q is Q-3; PA0 (14) Compounds of Preferred 10 where Q is Q-4; PA0 (15) Compounds of Preferred 10 where Q is Q-5; PA0 (16) Compounds of Preferred 10 where Q is Q-6; PA0 (17) Compounds of Preferred 10 where Q is Q-7; PA0 (18) Compounds of Preferred 10 where Q is Q-8; PA0 (19) Compounds of Preferred 10 where Q is Q-9; PA0 (20) Compounds of Preferred 10 where Q is Q-10; PA0 (21) Compounds of Preferred 10 where Q is Q-11; PA0 (22) Compounds of Preferred 10 where Q is Q-12; PA0 (23) Compounds of Preferred 10 where Q is Q-13; PA0 (24) Compounds of Preferred 10 where Q is Q-14; PA0 (25) Compounds of Preferred 10 where Q is Q-15; PA0 (26) Compounds of Preferred 10 where Q is Q-16; PA0 (27) Compounds of Preferred 10 where Q is Q-17; PA0 (28) Compounds of Preferred 10 where Q is Q-18; PA0 (29) Compounds of Preferred 10 where Q is Q-19; PA0 (30) Compounds of Preferred 10 where Q is Q-20; PA0 (31) Compounds of Preferred 10 where Q is Q-21; PA0 (32) Compounds of Preferred 10 where Q is Q-22; PA0 (33) Compounds of Preferred 10 where Q is Q-23; PA0 (34) Compounds of Preferred 10 where Q is Q-24; PA0 (35) Compounds of Preferred 10 where Q is Q-25; PA0 (36) Compounds of Preferred 10 where Q is Q-26; PA0 (37) Compounds of Preferred 10 where Q is Q-27; PA0 (38) Compounds of Preferred 10 where Q is Q-28; PA0 (39) Compounds of Preferred 10 where Q is Q-29; PA0 (40) Compounds of Preferred 10 where Q is Q-30; PA0 (41) Compounds of Preferred 10 where Q is Q-31; PA0 (42) Compounds of Preferred 10 where Q is Q-32; PA0 (43) Compounds of Preferred 10 where Q is Q-33; PA0 (44) Compounds of Preferred 10 where Q is Q-34; PA0 (45) Compounds of Preferred 10 where Q is Q-35; PA0 (46) Compounds of Preferred 10 where Q is Q-36; PA0 (47) Compounds of Preferred 10 where Q is Q-37; PA0 (48) Compounds of Preferred 10 where Q is Q-38; PA0 (49) Compounds of Preferred 10 where Q is Q-39; PA0 (50) Compounds of Preferred 10 where Q is Q-40; PA0 (51) Compounds of Preferred 10 where Q is Q-41; PA0 (52) Compounds of Preferred 10 where Q is Q-42; PA0 (53) Compounds of Preferred 10 where Q is Q-43; PA0 (54) Compounds of Preferred 10 where Q is Q-44; PA0 (55) Compounds of Preferred 10 where Q is Q-45; PA0 (56) Compounds of Preferred 10 where Q is Q-46; PA0 (57) Compounds of Preferred 10 where Q is Q-47; PA0 (58) Compounds of Preferred 10 where Q is Q-48; PA0 (59) Compounds of Preferred 10 where Q is Q-49; PA0 (60) Compounds of Preferred 10 where Q is Q-50; PA0 (61) Compounds of Preferred 10 where Q is Q-51; PA0 (62) Compounds of Preferred 10 where Q is Q-52; PA0 (63) Compounds of Preferred 10 where Q is Q-53; PA0 (64) Compounds of Preferred 10 where Q is Q-54; PA0 (65) Compounds of Preferred 10 where Q is Q-55; PA0 (66) Compounds of Preferred 10 where Q is Q-56; PA0 (67) Compounds of Preferred 10 where Q is Q-57; PA0 (68) Compounds of Preferred 10 where Q is Q-58; PA0 (69) Compounds of Preferred 10 where Q is Q-59; PA0 (70) Compounds of Preferred 10 where Q is Q-60; PA0 (71) Compounds of Preferred 10 where Q is Q-61; PA0 (72) Compounds of Preferred 10 where Q is Q-62; PA0 (73) Compounds of Preferred 10 where Q is Q-63; PA0 (74) Compounds of Preferred 10 where Q is Q-64; PA0 (75) Compounds of Preferred 10 where Q is Q-65; PA0 (76) Compounds of Preferred 10 where Q is Q-66; PA0 (77) Compounds of Preferred 10 where Q is Q-67; PA0 (78) Compounds of Preferred 10 where Q is Q-68; PA0 (79) Compounds of Preferred 10 where Q is Q-69; PA0 (80) Compounds of Preferred 10 where Q is Q-70; PA0 (81) Compounds of Preferred 10 where Q is Q-71; PA0 (82) Compounds of Preferred 10 where Q is Q-72; PA0 (83) Compounds of Preferred 10 where Q is Q-73; PA0 (84) Compounds of Preferred 10 where Q is Q-74; PA0 (85) Compounds of Preferred 10 where Q is Q-75; PA0 (86) Compounds of Preferred 10 where Q is Q-76; PA0 (87) Compounds of Preferred 10 where Q is Q-77; PA0 (88) Compounds of Preferred 10 where Q is Q-78; PA0 (89) Compounds of Preferred 10 where Q is Q-79; PA0 (90) Compounds of Preferred 10 where Q is Q-80; PA0 (91) Compounds of Preferred 10 where Q is Q-81; PA0 (92) Compounds of Preferred 10 where Q is Q-82; PA0 (93) Compounds of Preferred 10 where Q is Q-83; PA0 (94) Compounds of Preferred 10 where Q is Q-84; PA0 (95) Compounds of Preferred 10 where Q is Q-85; PA0 (96) Compounds of Preferred 10 where Q is Q-86; PA0 (97) Compounds of Preferred 10 where Q is Q-87; PA0 (98) Compounds of Preferred 10 where Q is Q-88; PA0 (99) Compounds of Preferred 10 where Q is Q-89; PA0 (100) Compounds of Preferred 10 where Q is Q-90; PA0 (101) Compounds of Preferred 10 where Q is Q-91; PA0 (102) Compounds of Preferred 10 where Q is Q-92; PA0 (103) Compounds of Preferred 10 where Q is Q-93; PA0 (104) Compounds of Preferred 10 where Q is Q-94; PA0 (105) Compounds of Preferred 10 where Q is Q-95; PA0 (106) Compounds of Preferred 10 where Q is Q-96; PA0 (107) Compounds of Preferred 10 where Q is Q-97; PA0 (108) Compounds of Preferred 10 where Q is Q-98; PA0 (109) Compounds of Preferred 10 where Q is Q-99; PA0 (110) Compounds of Preferred 10 where Q is Q-100; PA0 (111) Compounds of Preferred 10 where Q is Q-101; PA0 (112) Compounds of Preferred 10 where Q is Q-102; PA0 (113) Compounds of Preferred 10 where Q is Q-103; PA0 (114) Compounds of Preferred 10 where Q is Q-104; PA0 (115) Compounds of Preferred 10 where Q is Q-105; PA0 (116) Compounds of Preferred 10 where Q is Q-106; PA0 (117) Compounds of Preferred 10 where Q is Q-107; PA0 (118) Compounds of Preferred 10 where Q is Q-108; PA0 (119) Compounds of Preferred 10 where Q is Q-109; PA0 (120) Compounds of Preferred 10 where Q is Q-110; PA0 (121) Compounds of Preferred 10 where Q is Q-111; PA0 (122) Compounds of Preferred 10 where Q is Q-112; PA0 (123) Compounds of Preferred 10 where Q is Q-113; PA0 (124) Compounds of Preferred 10 where Q is Q-114; PA0 (125) Compounds of Preferred 10 where Q is Q-115; PA0 (126) Compounds of Preferred 10 where Q is Q-116; PA0 (127) Compounds of Preferred 10 where Q is Q-117; PA0 (128) Compounds of Preferred 10 where Q is Q-118; PA0 (129) Compounds of Preferred 10 where Q is Q-119; PA0 (130) Compounds of Preferred 10 where Q is Q-120; PA0 (131) Compounds of Preferred 10 where Q is Q-121; PA0 (132) Compounds of Preferred 10 where Q is Q-122; PA0 (133) Compounds of Preferred 10 where Q is Q-123; PA0 (134) Compounds of Preferred 10 where Q is Q-124; PA0 (135) Compounds of Preferred 10 where Q is Q-125; PA0 (136) Compounds of Preferred 10 where Q is Q-126; PA0 (137) Compounds of Preferred 10 where Q is Q-127; PA0 (138) Compounds of Preferred 10 where Q is Q-128; PA0 (139) Compounds of Preferred 10 where Q is Q-129; PA0 (140) Compounds of Preferred 10 where Q is Q-130; PA0 (141) Compounds of Preferred 10 where Q is Q-131; PA0 (142) Compounds of Preferred 10 where Q is Q-132; PA0 (143) Compounds of Preferred 10 where Q is Q-133; PA0 (144) Compounds of Preferred 10 where Q is Q-134; PA0 (145) Compounds of Preferred 10 where Q is Q-135; PA0 (146) Compounds of Preferred 10 where Q is Q-136; PA0 (147) Compounds of Preferred 10 where Q is Q-137; PA0 (148) Compounds of Preferred 10 where Q is Q-138; PA0 (149) Compounds of Preferred 10 where Q is Q-139; PA0 (150) Compounds of Preferred 10 where Q is Q-140; PA0 (151) Compounds of Preferred 10 where Q is Q-141; PA0 (152) Compounds of Preferred 10 where Q is Q-142; PA0 (153) Compounds of Preferred 10 where Q is Q-143; PA0 (154) Compounds of Preferred 10 where Q is Q-144; PA0 (155) Compounds of Preferred 10 where Q is Q-145; PA0 (156) Compounds of Preferred 10 where Q is Q-146; PA0 (157) Compounds of Preferred 10 where Q is Q-147; PA0 (158) Compounds of Preferred 10 where Q is Q-148; PA0 (159) Compounds of Preferred 10 where Q is Q-149; PA0 (160) Compounds of Preferred 10 where Q is Q-150; PA0 (161) Compounds of Preferred 10 where Q is Q-151; PA0 (162) Compounds of Preferred 10 where Q is Q-152; PA0 (163) Compounds of Preferred 10 where Q is Q-153; PA0 (164) Compounds of Preferred 10 where Q is Q-154; PA0 (165) Compounds of Preferred 10 where Q is Q-155; PA0 (166) Compounds of Preferred 10 where Q is Q-156; PA0 (167) Compounds of Preferred 10 where Q is Q-157; PA0 (168) Compounds of Preferred 10 where Q is Q-158; PA0 (169) Compounds of Preferred 10 where Q is Q-159; PA0 (170) Compounds of Preferred 10 where Q is Q-160; PA0 (171) Compounds of Preferred 10 where Q is Q-161; PA0 (172) Compounds of Preferred 10 where Q is Q-162; PA0 (173) Compounds of Preferred 10 where Q is Q-163; PA0 (174) Compounds of Preferred 10 where Q is Q-164; PA0 (175) Compounds of Preferred 10 where Q is Q-165; PA0 (176) Compounds of Preferred 10 where Q is Q-166. PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl-4-(tetrahydro-2-oxo furan-3-yl)pyrazole-3-sulfonamide; PA0 N-[(4-methoxy-6-methyltriazin-2-yl)aminocarbonyl]-1-methyl-4-(tetrahydro-2- oxofuran-3-yl)pyrazole-3-sulfonamide; and PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-methyl-4-(3-oxo-1-cyclohex enyl)-1H-pyrazole-5-sulfonamide, m.p. 175.degree.-182.degree. C. (dec).
South African Patent Application No. 83/8416 (published May, 1984) discloses herbicidal benzenesulfonamides of formula ##STR3## wherein A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms.
EP-A-95,925 (published Dec. 7, 1983) discloses herbicidal pyrazolesulfonamides in which the group adjacent to the sulfonamide moiety may be selected from H, C.sub.1 -C.sub.3 alkyl, F, Cl, Br, NO.sub.2, OR.sub.16, CO.sub.2 R.sub.23, S(O).sub.n R.sub.24 or SO.sub.2 NR.sub.19 R.sub.20.
EP-A-87,780 (published Sept. 7, 1983) claims pyrazole sulfonamides of general formula ##STR4## wherein A is H, C.sub.1 -C.sub.8 alkyl or optionally substituted phenyl;
EP-A-96,003 (published Nov. 28, 1983) discloses herbicidal compounds of general formula ##STR5## wherein R.sub.1 is H or C.sub.1 -C.sub.3 alkyl; and
Unexamined Japanese Patent Application No. 9,013,778 (priority July 15, 1982) filed by Nihon Noyaku describes herbicidal pyrazolesulfonamides with halo, alkyl and alkoxycarbonyl substituents.
European Publication No. 116,518 (published 8/22/84; Swiss priority 2/4/83) discloses herbicidal sulfonylureas of the formula ##STR6## where, in part, X is --NR.sub.6 R.sub.7, --N(SO.sub.2 R.sub.9).sub.2 or ##STR7## A is --CO--, --SO.sub.2 --, --CONR.sub.23 -- or --CO.sub.2 --; B is C.sub.1 -C.sub.4 alkylene or C.sub.2 -C.sub.4 alkenylene;